A Checklist for Someone About to Take on a Tougher Job

Careers involve numerous transitions when we “step up” into a new role, typically one with greater rewards, bigger responsibilities, and higher stakes. We’re well aware that these opportunities come as the result of effort and diligence in our previous role, but we can fail to appreciate how much hard work is required after we’ve made the transition to ensure that it’s a successful one. The senior leaders in my coaching practice and my MBA students at Stanford are often in the midst of one of these transitions, and my work with them has highlighted a set of issues that we should address when stepping up, along with a corresponding set of critical questions to ask along the way as a kind of “stepping up checklist.”

A New Culture

New opportunities often require us to step into a new organizational culture. Even when we’re staying within the same company, we may be moving into a new sub-culture, where the formal signs and artifacts look the same, but their informal meanings and interpretations are quite different.

By definition, when we step up we’ve enjoyed success in our previous culture—and yet the personal qualities and behaviors that were rewarded in our old environment may not be the qualities and behaviors that will rewarded in our new environment. Presumably we anticipate that the new culture will be a good fit, but it’s tremendously difficult to assess a culture until we’re actually working within it. Most of my clients are start-up CEOs who vet senior hires scrupulously, and yet the most common cause of failure at the executive level in their companies is “poor cultural fit.” An otherwise talented person simply couldn’t adapt to a new way of working with others. Before stepping up, consider:

How would we characterize our previous organizational culture—and how has that culture influenced us?

How would we characterize the culture we’re entering?

What might feel different in the new culture—and how might we turn those differences to our advantage?

What might we miss about the old culture—and how might we compensate for those changes?

How can we get feedback on our efforts to adapt to the new culture?

How might we influence the new culture to adapt to us?

Stretching

Just as we can miss the subtleties of a new organizational culture and fail to adapt, we can mistakenly assume that we’re being asked to do more of what led us to succeed in the past and miss opportunities to stretch. Upward moves into different professions, different industries or significantly different roles obviously require us to stretch ourselves—and yet most of the time when we’re stepping up the nature of the transition isn’t quite so obvious.

There’s generally a great deal of continuity between roles when we set up, but it’s important to look for the differences and to anticipate where they will challenge us.

In what ways does this new opportunity differ from our previous role?

More specifically, how might the new opportunity look similar but actually be different?

How will those differences require us to stretch beyond our comfort zone? How far are we prepared to go? How far is too far?

What support will we need to stretch ourselves successfully?

Onboarding

Typically the more senior the role, the less structured the onboarding process, and this is particularly true in startups and other small enterprises. This can feel liberating when we’re prepared for it, but it can feel disorienting if it comes as a surprise. The key is to think like an organization and take responsibility for our own onboarding.

This doesn’t mean we must go it alone without asking for help or accepting support—far from it. But we should expect to encounter more uncertainty and ambiguity in our new environment than we’re used to, and we should be prepared to get up to speed as independently as possible.

What do we need to do in the first week? The first 30 days? The first quarter?

Who do we need to meet, and what’s the best way to connect with them?

What don’t we know—and what will we be expected to know?

If we find ourselves struggling, how will we ask for help or guidance?

Self-Care

Sufficient sleep, regular exercise, a healthy diet, and some form of mindfulness practice, such as meditation are the essential building blocks of self-care. I talk about every one of these issues with my clients, because at more senior levels optimum performance isn’t the result of intellectual horsepower or longer hours in the office—everyone’s super-smart and everyone’s working hard. Rather, it’s about being in the best possible mental, emotional and physical condition to maximize our focused attention and to support effective decision-making and interpersonal interactions.

The challenge is that the heightened pressure that often accompanies a step up leads us to neglect these issues and devote even less time to self-care, just when we need it most. It can be helpful to bear in mind that self-care isn’t an indulgence—it’s an investment in our own effectiveness—and the more senior we are, the more important it is that we function at our best. In addition to the considerations below, use an extremely simple tool — I like Don’t Break the Chain – to track daily activities, such as exercise or a good night’s sleep. Avoid the temptation to make this process too complex.

What are our most effective self-care routines, and how might we keep these routines intact?

What routines do we struggle to maintain—and how might we get some help?

Professional Development

Finally, stepping up means taking ownership of our long-term development as professionals. High-performers often enjoy the benefit of managers who steer us toward developmental opportunities and mentors who take a special interest in our growth. But the higher we rise, the less we can depend on someone more senior to guide us.

The best advice I got when I began reporting to a board of directors in my first job after business school was to remember that the board would not be responsible for my professional development as my previous managers had been. I continued to benefit from the support of mentor figures, both on my board and from previous roles, but as the leader of the organization, the only person who could be responsible for my future growth was me.

The good news is that while more senior roles provide less structure for ongoing professional development, they often provide more resources, such as financial support for executive coaching, or greater flexibility, allowing time for reflection away from tactical duties.

What developmental resources are available to us in this role?

What resources might be made available if we asked for them?

How might we sustain those informal relationships—or cultivate new ones—with people who have an interest in our continued development?